Natural Product: NPC471149

Natural Product ID:  NPC471149
Common Name:   4,6-Di-O-Acetylchamissonolide
IUPAC Name:   [(3aR,5R,5aS,6S,8R,8aS,9S,9aR)-8,9-diacetyloxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] acetate
Synonyms:  
Molecular Formula:   C21H28O8
Standard InCHIKey:  ZXJZGYQBAFUERW-BRLYISDVSA-N
Standard InCHI:  InChI=1S/C21H28O8/c1-9-7-14-17(10(2)20(25)29-14)19(28-13(5)24)21(6)16(27-12(4)23)8-15(18(9)21)26-11(3)22/h9,14-19H,2,7-8H2,1,3-6H3/t9-,14-,15+,16-,17-,18-,19+,21-/m1/s1
Canonical SMILES:  CC(=O)O[C@H]1C[C@H]([C@@]2([C@@H]1[C@H](C)C[C@@H]1[C@H]([C@@H]2OC(=O)C)C(=C)C(=O)O1)C)OC(=O)C
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO9829 Arnica chamissonis Species Asteraceae Eukaryota PMID[23501116]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 > 30000 nM 9514009
NPT840 Individual Protein Transcriptional activator Myb Gallus gallus IC50 = 12970 nM DrugMatrix in vitro pharmacology data
NPT840 Individual Protein Transcriptional activator Myb Gallus gallus IC50 = 12971.79 nM 19654408

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC471149 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.988 High Similarity NPC283409
0.9878 High Similarity NPC24728
0.9419 High Similarity NPC35959
0.9419 High Similarity NPC133888
0.9419 High Similarity NPC29821
0.9419 High Similarity NPC57304
0.9419 High Similarity NPC171360
0.9419 High Similarity NPC63193
0.9419 High Similarity NPC293001
0.9302 High Similarity NPC35809
0.9302 High Similarity NPC297474
0.9302 High Similarity NPC54065
0.9286 High Similarity NPC304558
0.9268 High Similarity NPC246076
0.9195 High Similarity NPC286341
0.9195 High Similarity NPC191339
0.9186 High Similarity NPC155935
0.9186 High Similarity NPC472872
0.9 High Similarity NPC24956
0.9 High Similarity NPC18019
0.8864 High Similarity NPC216284
0.8851 High Similarity NPC79549
0.8851 High Similarity NPC207114
0.8851 High Similarity NPC217983
0.8837 High Similarity NPC56593
0.8837 High Similarity NPC64153
0.8791 High Similarity NPC142529
0.8791 High Similarity NPC91771
0.8764 High Similarity NPC155215
0.875 High Similarity NPC215556
0.8706 High Similarity NPC54468
0.8681 High Similarity NPC472873
0.8681 High Similarity NPC476053
0.8667 High Similarity NPC258216
0.8667 High Similarity NPC473234
0.8667 High Similarity NPC473263
0.8667 High Similarity NPC60386
0.8667 High Similarity NPC472874
0.8667 High Similarity NPC308656
0.8667 High Similarity NPC473273
0.8652 High Similarity NPC19087
0.8621 High Similarity NPC187661
0.8621 High Similarity NPC238593
0.8571 High Similarity NPC127019
0.8556 High Similarity NPC184063
0.8539 High Similarity NPC38392
0.8523 High Similarity NPC270270
0.8506 High Similarity NPC204105
0.8506 High Similarity NPC300082
0.8506 High Similarity NPC284534
0.8506 High Similarity NPC235792
0.8495 Intermediate Similarity NPC471150
0.8495 Intermediate Similarity NPC311904
0.8478 Intermediate Similarity NPC213698
0.8478 Intermediate Similarity NPC167893
0.8478 Intermediate Similarity NPC163228
0.8471 Intermediate Similarity NPC47635
0.8462 Intermediate Similarity NPC153590
0.8462 Intermediate Similarity NPC200237
0.8427 Intermediate Similarity NPC224652
0.8421 Intermediate Similarity NPC171759
0.8391 Intermediate Similarity NPC194859
0.8391 Intermediate Similarity NPC224386
0.8387 Intermediate Similarity NPC213078
0.837 Intermediate Similarity NPC473331
0.8353 Intermediate Similarity NPC6823
0.8353 Intermediate Similarity NPC293418
0.8353 Intermediate Similarity NPC290508
0.8353 Intermediate Similarity NPC73052
0.8352 Intermediate Similarity NPC475925
0.8316 Intermediate Similarity NPC186861
0.8315 Intermediate Similarity NPC118601
0.8315 Intermediate Similarity NPC201658
0.8298 Intermediate Similarity NPC213947
0.8298 Intermediate Similarity NPC161493
0.8298 Intermediate Similarity NPC108475
0.8298 Intermediate Similarity NPC170143
0.8293 Intermediate Similarity NPC320537
0.8293 Intermediate Similarity NPC143979
0.828 Intermediate Similarity NPC67584
0.828 Intermediate Similarity NPC170120
0.8276 Intermediate Similarity NPC111409
0.8276 Intermediate Similarity NPC245665
0.8276 Intermediate Similarity NPC128246
0.8222 Intermediate Similarity NPC178875
0.8211 Intermediate Similarity NPC45125
0.8172 Intermediate Similarity NPC198853
0.8152 Intermediate Similarity NPC133698
0.8132 Intermediate Similarity NPC4986
0.8132 Intermediate Similarity NPC12872
0.8132 Intermediate Similarity NPC168679
0.8125 Intermediate Similarity NPC471381
0.8105 Intermediate Similarity NPC474313
0.8105 Intermediate Similarity NPC181151
0.8085 Intermediate Similarity NPC52044
0.8085 Intermediate Similarity NPC224689
0.8046 Intermediate Similarity NPC126248
0.8021 Intermediate Similarity NPC249171
0.8021 Intermediate Similarity NPC221615
0.8021 Intermediate Similarity NPC49833
0.8 Intermediate Similarity NPC208223
0.8 Intermediate Similarity NPC236692
0.8 Intermediate Similarity NPC309757
0.8 Intermediate Similarity NPC126156
0.8 Intermediate Similarity NPC67493
0.7979 Intermediate Similarity NPC470010
0.7979 Intermediate Similarity NPC323008
0.7979 Intermediate Similarity NPC477131
0.7979 Intermediate Similarity NPC262133
0.7979 Intermediate Similarity NPC470013
0.7957 Intermediate Similarity NPC131209
0.7957 Intermediate Similarity NPC221282
0.7931 Intermediate Similarity NPC156658
0.7931 Intermediate Similarity NPC258965
0.7917 Intermediate Similarity NPC236580
0.7917 Intermediate Similarity NPC304445
0.79 Intermediate Similarity NPC54737
0.7879 Intermediate Similarity NPC473148
0.7865 Intermediate Similarity NPC128429
0.7857 Intermediate Similarity NPC150923
0.7849 Intermediate Similarity NPC301969
0.7849 Intermediate Similarity NPC37607
0.7849 Intermediate Similarity NPC475776
0.7843 Intermediate Similarity NPC139838
0.7843 Intermediate Similarity NPC59489
0.7826 Intermediate Similarity NPC91248
0.7816 Intermediate Similarity NPC182550
0.781 Intermediate Similarity NPC471382
0.7805 Intermediate Similarity NPC5714
0.7802 Intermediate Similarity NPC162071
0.7802 Intermediate Similarity NPC107787
0.7802 Intermediate Similarity NPC470242
0.7789 Intermediate Similarity NPC281775
0.7778 Intermediate Similarity NPC80144
0.7778 Intermediate Similarity NPC156485
0.7778 Intermediate Similarity NPC115786
0.7766 Intermediate Similarity NPC70595
0.7766 Intermediate Similarity NPC123177
0.7766 Intermediate Similarity NPC74103
0.7766 Intermediate Similarity NPC150978
0.7766 Intermediate Similarity NPC290651
0.7727 Intermediate Similarity NPC74673
0.7727 Intermediate Similarity NPC69271
0.7727 Intermediate Similarity NPC276356
0.7723 Intermediate Similarity NPC44004
0.7723 Intermediate Similarity NPC291643
0.7717 Intermediate Similarity NPC190753
0.7717 Intermediate Similarity NPC175293
0.7708 Intermediate Similarity NPC304886
0.77 Intermediate Similarity NPC221421
0.7692 Intermediate Similarity NPC78089
0.7684 Intermediate Similarity NPC135776
0.7684 Intermediate Similarity NPC475788
0.7677 Intermediate Similarity NPC471767
0.7677 Intermediate Similarity NPC67296
0.7667 Intermediate Similarity NPC215294
0.7664 Intermediate Similarity NPC36754
0.766 Intermediate Similarity NPC253144
0.7653 Intermediate Similarity NPC470188
0.7647 Intermediate Similarity NPC26617
0.7647 Intermediate Similarity NPC470192
0.7642 Intermediate Similarity NPC471380
0.764 Intermediate Similarity NPC281949
0.764 Intermediate Similarity NPC25684
0.764 Intermediate Similarity NPC301477
0.7629 Intermediate Similarity NPC113433
0.7629 Intermediate Similarity NPC474297
0.7629 Intermediate Similarity NPC476009
0.7609 Intermediate Similarity NPC50637
0.7604 Intermediate Similarity NPC471446
0.7604 Intermediate Similarity NPC474841
0.7604 Intermediate Similarity NPC473434
0.76 Intermediate Similarity NPC78127
0.76 Intermediate Similarity NPC471757
0.76 Intermediate Similarity NPC250594
0.76 Intermediate Similarity NPC105725
0.7596 Intermediate Similarity NPC471884
0.7593 Intermediate Similarity NPC161060
0.7586 Intermediate Similarity NPC470240
0.7586 Intermediate Similarity NPC476794
0.7582 Intermediate Similarity NPC470238
0.7582 Intermediate Similarity NPC138647
0.7579 Intermediate Similarity NPC284185
0.7576 Intermediate Similarity NPC70865
0.7573 Intermediate Similarity NPC68248
0.7558 Intermediate Similarity NPC471491
0.7553 Intermediate Similarity NPC92974
0.7553 Intermediate Similarity NPC288699
0.7551 Intermediate Similarity NPC261372
0.7551 Intermediate Similarity NPC58267
0.7551 Intermediate Similarity NPC477949
0.7551 Intermediate Similarity NPC263674
0.7549 Intermediate Similarity NPC223450
0.7547 Intermediate Similarity NPC273242
0.7528 Intermediate Similarity NPC474981
0.7528 Intermediate Similarity NPC51507
0.7527 Intermediate Similarity NPC186148
0.7527 Intermediate Similarity NPC5130
0.7526 Intermediate Similarity NPC280877
0.7526 Intermediate Similarity NPC259042

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC471149 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8132 Intermediate Similarity NPD1695 Approved
0.7647 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD6371 Approved
0.7053 Intermediate Similarity NPD4249 Approved
0.6979 Remote Similarity NPD4250 Approved
0.6979 Remote Similarity NPD4251 Approved
0.6947 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6939 Remote Similarity NPD5785 Approved
0.6887 Remote Similarity NPD6008 Approved
0.6818 Remote Similarity NPD6053 Discontinued
0.6632 Remote Similarity NPD6435 Approved
0.6632 Remote Similarity NPD4752 Clinical (unspecified phase)
0.66 Remote Similarity NPD46 Approved
0.66 Remote Similarity NPD6698 Approved
0.6598 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6598 Remote Similarity NPD1694 Approved
0.6596 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6569 Remote Similarity NPD5282 Discontinued
0.6566 Remote Similarity NPD6903 Approved
0.6562 Remote Similarity NPD5362 Discontinued
0.6531 Remote Similarity NPD5330 Approved
0.6531 Remote Similarity NPD7521 Approved
0.6531 Remote Similarity NPD6684 Approved
0.6531 Remote Similarity NPD7334 Approved
0.6531 Remote Similarity NPD6409 Approved
0.6531 Remote Similarity NPD7146 Approved
0.6476 Remote Similarity NPD7638 Approved
0.6455 Remote Similarity NPD6686 Approved
0.6429 Remote Similarity NPD5363 Approved
0.6421 Remote Similarity NPD4822 Approved
0.6421 Remote Similarity NPD4820 Approved
0.6421 Remote Similarity NPD4821 Approved
0.6421 Remote Similarity NPD4819 Approved
0.6421 Remote Similarity NPD5368 Approved
0.6415 Remote Similarity NPD7639 Approved
0.6415 Remote Similarity NPD7640 Approved
0.64 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6392 Remote Similarity NPD7154 Phase 3
0.6383 Remote Similarity NPD4271 Approved
0.6383 Remote Similarity NPD4268 Approved
0.6373 Remote Similarity NPD5693 Phase 1
0.6354 Remote Similarity NPD5369 Approved
0.6346 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6311 Remote Similarity NPD6399 Phase 3
0.6289 Remote Similarity NPD4269 Approved
0.6289 Remote Similarity NPD4270 Approved
0.6289 Remote Similarity NPD5209 Approved
0.6275 Remote Similarity NPD5207 Approved
0.6275 Remote Similarity NPD7838 Discovery
0.6216 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6214 Remote Similarity NPD8035 Phase 2
0.6214 Remote Similarity NPD8034 Phase 2
0.62 Remote Similarity NPD5786 Approved
0.619 Remote Similarity NPD5695 Phase 3
0.6174 Remote Similarity NPD8133 Approved
0.6168 Remote Similarity NPD4225 Approved
0.6168 Remote Similarity NPD5696 Approved
0.6148 Remote Similarity NPD7507 Approved
0.614 Remote Similarity NPD6650 Approved
0.614 Remote Similarity NPD6649 Approved
0.6106 Remote Similarity NPD6372 Approved
0.6106 Remote Similarity NPD6373 Approved
0.6095 Remote Similarity NPD6001 Approved
0.6082 Remote Similarity NPD4252 Approved
0.6078 Remote Similarity NPD6672 Approved
0.6078 Remote Similarity NPD5737 Approved
0.6075 Remote Similarity NPD6084 Phase 2
0.6075 Remote Similarity NPD6083 Phase 2
0.6071 Remote Similarity NPD5697 Approved
0.6071 Remote Similarity NPD6412 Phase 2
0.6061 Remote Similarity NPD5331 Approved
0.6061 Remote Similarity NPD5332 Approved
0.6058 Remote Similarity NPD7983 Approved
0.6053 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6042 Remote Similarity NPD5784 Clinical (unspecified phase)
0.602 Remote Similarity NPD4790 Discontinued
0.6019 Remote Similarity NPD6673 Approved
0.6019 Remote Similarity NPD6904 Approved
0.6019 Remote Similarity NPD6051 Approved
0.6019 Remote Similarity NPD6080 Approved
0.6018 Remote Similarity NPD7320 Approved
0.6018 Remote Similarity NPD6899 Approved
0.6018 Remote Similarity NPD6881 Approved
0.6 Remote Similarity NPD7319 Approved
0.6 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6 Remote Similarity NPD6319 Approved
0.6 Remote Similarity NPD7632 Discontinued
0.5982 Remote Similarity NPD6675 Approved
0.5982 Remote Similarity NPD7128 Approved
0.5982 Remote Similarity NPD6402 Approved
0.5982 Remote Similarity NPD5739 Approved
0.5965 Remote Similarity NPD6013 Approved
0.5965 Remote Similarity NPD6014 Approved
0.5965 Remote Similarity NPD6012 Approved
0.5962 Remote Similarity NPD5692 Phase 3
0.595 Remote Similarity NPD8033 Approved
0.5948 Remote Similarity NPD6882 Approved
0.5948 Remote Similarity NPD8297 Approved
0.5935 Remote Similarity NPD7492 Approved
0.5934 Remote Similarity NPD229 Approved
0.5929 Remote Similarity NPD5701 Approved
0.5922 Remote Similarity NPD5208 Approved
0.5914 Remote Similarity NPD5777 Approved
0.5913 Remote Similarity NPD6883 Approved
0.5913 Remote Similarity NPD7102 Approved
0.5913 Remote Similarity NPD7290 Approved
0.5905 Remote Similarity NPD5284 Approved
0.5905 Remote Similarity NPD7637 Suspended
0.5905 Remote Similarity NPD5694 Approved
0.5905 Remote Similarity NPD6050 Approved
0.5905 Remote Similarity NPD5281 Approved
0.59 Remote Similarity NPD4788 Approved
0.5897 Remote Similarity NPD4632 Approved
0.5895 Remote Similarity NPD8039 Approved
0.5893 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5893 Remote Similarity NPD4057 Clinical (unspecified phase)
0.5887 Remote Similarity NPD6616 Approved
0.5882 Remote Similarity NPD7115 Discovery
0.5882 Remote Similarity NPD6098 Approved
0.5877 Remote Similarity NPD6011 Approved
0.5876 Remote Similarity NPD4802 Phase 2
0.5876 Remote Similarity NPD4238 Approved
0.5872 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5868 Remote Similarity NPD6054 Approved
0.5862 Remote Similarity NPD6847 Approved
0.5862 Remote Similarity NPD8130 Phase 1
0.5862 Remote Similarity NPD6617 Approved
0.5862 Remote Similarity NPD6869 Approved
0.5859 Remote Similarity NPD6845 Suspended
0.5849 Remote Similarity NPD5778 Approved
0.5849 Remote Similarity NPD5779 Approved
0.5842 Remote Similarity NPD3666 Approved
0.5842 Remote Similarity NPD3133 Approved
0.5842 Remote Similarity NPD3665 Phase 1
0.584 Remote Similarity NPD7078 Approved
0.5833 Remote Similarity NPD7327 Approved
0.5833 Remote Similarity NPD7328 Approved
0.5826 Remote Similarity NPD4061 Clinical (unspecified phase)
0.582 Remote Similarity NPD6016 Approved
0.582 Remote Similarity NPD6015 Approved
0.5804 Remote Similarity NPD6052 Approved
0.5794 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5794 Remote Similarity NPD7900 Approved
0.5794 Remote Similarity NPD7736 Approved
0.5785 Remote Similarity NPD7516 Approved
0.5784 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5781 Remote Similarity NPD7260 Phase 2
0.5772 Remote Similarity NPD5988 Approved
0.5772 Remote Similarity NPD6370 Approved
0.5766 Remote Similarity NPD1700 Approved
0.5755 Remote Similarity NPD6411 Approved
0.575 Remote Similarity NPD6009 Approved
0.5747 Remote Similarity NPD3198 Approved
0.5741 Remote Similarity NPD5210 Approved
0.5741 Remote Similarity NPD4629 Approved
0.5739 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5738 Remote Similarity NPD6059 Approved
0.5738 Remote Similarity NPD8294 Approved
0.5738 Remote Similarity NPD8377 Approved
0.5714 Remote Similarity NPD8293 Discontinued
0.5714 Remote Similarity NPD4753 Phase 2
0.5714 Remote Similarity NPD5211 Phase 2
0.5691 Remote Similarity NPD5983 Phase 2
0.5691 Remote Similarity NPD8378 Approved
0.5691 Remote Similarity NPD7503 Approved
0.5691 Remote Similarity NPD8380 Approved
0.5691 Remote Similarity NPD8335 Approved
0.5691 Remote Similarity NPD8379 Approved
0.5691 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5691 Remote Similarity NPD8296 Approved
0.5686 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5686 Remote Similarity NPD3668 Phase 3
0.5676 Remote Similarity NPD6648 Approved
0.5676 Remote Similarity NPD5285 Approved
0.5676 Remote Similarity NPD5286 Approved
0.5676 Remote Similarity NPD4696 Approved
0.5667 Remote Similarity NPD6274 Approved
0.5652 Remote Similarity NPD6685 Approved
0.5644 Remote Similarity NPD3667 Approved
0.5636 Remote Similarity NPD7902 Approved
0.5636 Remote Similarity NPD4755 Approved
0.5625 Remote Similarity NPD5344 Discontinued
0.5614 Remote Similarity NPD5141 Approved
0.5604 Remote Similarity NPD9496 Clinical (unspecified phase)
0.5604 Remote Similarity NPD2685 Clinical (unspecified phase)
0.56 Remote Similarity NPD7604 Phase 2

Structure

External Identifiers

PubChem CID   73356470
ChEMBL   CHEMBL2380799
ZINC  

Physicochemical Properties

Molecular Weight:  408.18
ALogP:  0.0084
MLogP:  2.89
XLogP:  2.466
# Rotatable Bonds:  11
Polar Surface Area:  105.2
# H-Bond Aceptor:  8
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  29

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs